2-Fluoro-4-formylbenzonitrile → 2-Fluoro-4-(1-hydroxyethyl)benzonitrile

Temperature

-78 °C

To a solution of 4-cyano-3-fluorobenzaldehyde, as described above in Step B, (250 mg, 1.68 mmol) in THF, under argon, at −78° C. was added MeMgBr dropwise (0.59 mL of a 3.0 M solution in Et2O, 1.77 mmol). The reaction mixture was stirred at −78° C. for 1 hour, then quenched with saturated aqueous NH4Cl, allowed to warm to ambient temperature, and extracted with CH2Cl2 (2×40 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of hexane—20% to 40% EtOAc, to yield the titled product as a white solid.

1. customquenched with saturated aqueous NH4Cl
2. temperatureto warm to ambient temperature
3. extractionextracted with CH2Cl2 (2×40 mL)
4. dry with materialThe combined organic extracts were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel chromatography
8. washeluting with a gradient of hexane—20% to 40% EtOAc

ORD record

ord-5bcecdb43dcf4d31ad982310d82270a4

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441017B1